Certain 1-phenyl-1-oxygen heterocyclic carbonyloxy ureas

ABSTRACT

1. A COMPOUND OF THE FORMULA   (H(5-N)-),X(N)-PHENYL-N(-OOC-Y)-CO-N(-R1)-R2   WHEREIN X IS SELECTED FROM THE GROUP CONSISTING OF LOWER ALKYL, LOWER ALKENYL, CHLORINE, BROMINE, LOWER HALOALKYL, LOWER ALKOXY, NITRO AND DI(LOWER ALKYL)AMINO; N IS AN INTEGER FROM 0 TO 3; R1 AND R2 ARE INDEPENDENTLY SELECTED FROM THE GROUP CONSISTING OF HYDROGEN AND LOWER ALKYL; AND Y IS A SUBSTITUTED OR UNSUBSTITUTED HETEROCYCLIC RING CONSISTING OF FURAN AND TETRAHYDROFURAN WHEREIN SUBSTITUENTS ARE SELECTED FROM THE GROUP CONSISTING OF LOWER ALKYL, CHLORINE AND BROMINE.

United States Patent 3,840,564 CERTAIN l-PHENYL-l-OXYGEN HETEROCYCLIC'CARBONYLOXY UREAS John Krenzer, Oak Park, and Sidney B. Richter,Chicago,

Ill., assignors to Velsicol Chemical Corporation, Chicago, II].

No Drawing. Continuation of abandoned application Ser. No. 781,578, Dec.5, 1968. This application Feb. 16, 1972, Ser. No. 226,964

Int. Cl. C07d /16 US. Cl. 260-3473 2 Claims ABSTRACT OF THE DISCLOSUREThis invention discloses new chemical compounds of the formula wherein Xis selected from the group consisting of alkyl, alkenyl, halogen,haloalkyl, alkoxy, nitro and dialkylamino; n is an integer from 0 to 5;R and R are independently selected from the group consisting of hydrogenand alkyl; and Y is a substituted or unsubstituted heterocyclic ringconsisting of from 3 to 5 carbon atoms and a maximum of 1 atom selectedfrom the group consisting of oxygen, sulfur and nitrogen wherein thesubstituents are selected from the group consisting of alkyl andhalogen. The compounds of this invention are useful as herbicides.

This is a continuation of application Ser. No. 781,578, filed Dec. 5,1968, now abandoned.

This invention relates to new compositions of matter and moreparticularly to new chemical compounds of the formula wherein X isselected from the group consisting of alkyl, alkenyl, halogen,haloalkyl, alkoxy, nitro and dialkylamino; n is an integer from 0 to 5;R and R are independently selected from the group consisting of hydrogenand alkyl; and Y is a substituted or unsubstituted heterocyclic ringconsisting of from 3 to 5 carbon atoms and a maximum of 1 atom selectedfrom the group consisting of oxygen, sulfur and nitrogen wherein thesubstituents are selected from the group consisting of alkyl andhalogen.

In a preferred embodiment of this invention X is selected from the groupconsisting of lower alkyl, lower alkenyl, chlorine, bromine, lowerhaloalkyl, lower alkoxy, nitro and di(lower alkyl)amino; n is an integerfrom 0 to 3; R and R are independently selected from the groupconsisting of hydrogen and lower alkyl; and Y is a substituted orunsubstituted heterocyclic ring selected from the group consisting ofpyrrole, furan, tetrahydrofuran, thiophene, tetrahydrothiophene,pyridine and tetrahydropyran wherein the substituents are selected fromthe group consisting of lower alkyl, chlorine and bromine.

The compounds of the present invention are unexpectedly useful asherbicides.

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The new compounds of the present invention can be readily prepared byreacting a hydroxyurea of the formula wherein X, n, R and R are asheretofore described, with an acid chloride of the formula wherein Y isas heretofore described. This reaction can be conveniently carried outin an inert organic reaction medium such as ether by adding an equimolaror slight excess molar amount of the acid chloride of Formula III to thehydroxyurea of Formula II in the presence of an acid scavenger such as atertiary amine or an alkali metal hydroxide. Mild reaction conditionscan be employed to efiect this reaction and temperatures from about 0 C.to about 50 C. are preferably utilized. The reaction mixture can then bestirred for a period of from about /2 to about 8 hours to ensure thecompletion of the reaction. Thereafter the desired product can berecovered by first filtering the reaction mixture to remove the acidscavenger chloride salt and then evaporating the filtrate to yield thedesired product as a residue. In some instances wherein the product isinsoluble in the reaction medium and forms as a precipitate it isrecovered by filtration and is purified by washing with water. Theproduct can then be used as such or can be further purified byconventional techniques well known in the art.

Exemplary suitable hydroxyureas for the purpose of preparing the newcompounds of this invention are l-hydroxy- 1 -phenylurea,1-hydroxy-1-phenyl-3 -methylurea, l-hydroxy-1-phenyl-3,3-dimethylurea,l-hydroxyl (Z-methylphenyl -3 -methylurea, l-hydroxy- 1- 3-chlorophenyl) -3 -methylurea,1-hyd.roxy-1-(3,4-dichlorophenyl)-3-methylurea, l-hydroxy- 1-4-bromophenyl) -3,3-dimethylurea,l-hydroxy-1-(4-allylphenyl)-3-ethylurea,l-hydroxy-1-(2-methoxyphenyl)-3-isopropylurea, l-hydroxy-1-(3-nitrophenyl) -3-methylurea, l-hydroxy- 1- (2-dimethylaminophenyl)-3-methylurea, l-hydroxy- 1- (2-methyl-4-chlorophenyl)-3,3-dimethylurea, l-hydroxyl- 3,4,5 -trichlorophenyl -3,3-diethylureaand l-hydroxy- 1- 4-chloropheny1 -3-methyl-3-t-butylurea.

Exemplary suitable heterocyclic acid chlorides for preparing thecompounds of this invention are a-furoyl chloride, fi-furoyl chloride,a-thiophenoyl chloride, fi-thiophenoyl chloride, tetrahydropyran 4carboxyloyl chloride, picolinoyl chloride, nicotinoyl chloride andisonicotinoyl chloride.

The manner in which the compounds of the present invention can beprepared readily is more specifically illustrated in the followingexamples.

EXAMPLE 1 Preparation of 1- 3 ,4-dichloropheny1)- 1-(a-furoyloxy)-3-methylurea 1-(3,4-dichlorophenyl) 1 hydroxy- 3 methylurea (5 grams)dissolved in dichloromethane ml.) and triethylarnine (4 ml.) werecharged into a glass reaction vessel equipped with a mechanical stirrer.The mixture was cooled to a temperature of about 10 C. and u-furoylchloride (2.9 grams) was added thereto. After the addition was completedthe reaction mixture was stirred for a period of about /2 hour. Thereaction mixture was then washed with water and was dried over anhydrousmagnesium sulfate. The dried solution was stripped of solvent and theresulting residue was recrystallized from methanol to yield the desiredproduct 1-(3,4-dichlorophenyl)-1- (a-furoyloxy)-3-methylurea as a tancrystalline solid having a melting point of 104 to 105 C.

EXAMPLE 2 Preparation of 1-(2-methyl-4-chlorophenyl)-1-(a-pyrrolylcarbonyloxy-3-ethylurea A solution of1-(2-methyl-4-chlorophenyl)-1-hydroxy- 3-ethylurea (23 grams; 0.1 mol)in chloroform (150 ml.) and triethylamine (11 grams) are charged into aglass reaction vessel equipped with a mechanical stirrer. The

mixture is cooled to a temperature of about C. and u-pyrrolylcarbonylchloride (10.6 grams; 0.1 mol) is slowly added thereto. After theaddition is completed the mixture is stirred for an additional period ofabout 1 hour. After this time the reaction mixture is filtered to removethe triethylamine hydrochloride, is washed with water and is dried overanhydrous magnesium sulfate. The dried solution is then stripped ofsolvent and the resulting residue is recrystallized to yield the desiredproduct 1-(2-methyl-4-chlorophenyl)-1-(u pyrrolylcarbonyloxy)-3-ethylurea.

EXAMPLE 3 Preparation of 1(3bromophenyl)-1- a-thenoyloxy) -3,3-dimethylurea A solution of1-(3-bromophenyl)-1-hydroxy-3,3-dimethylurea (24.7 grams; 0.1 mol) indichloromethane (100 ml.) and triethylamine (11 grams) are charged intoa glass reaction vessel equipped with a mechanical stirrer. The mixtureis cooled to a temperature of about 5 C. and a-thenoyl chloride is lowlyadded thereto. After the addition is completed the reaction mixture iswarmed to room temperature and is stirred for a period of about 1 hour.After this time the mixture is filtered to remove the triethylaminehydrochloride, is washed with water and is dried over anhydrousmagnesium sulfate. The dried solution is then stripped of solvent andthe resulting residue is recrystallized to yield the desired product1-(3-bromophenyl) -1- a-thenoyloxy) -3 ,3 -dimethylurea EXAMPLE 4Preparation of 1-(2-methoxy-4-chlorophenyl)-1-(4-tetrahydropyranylcarbonyloxy) -3-methylurea A solution of1-(2-methoxy-4-chlorophenyl)-l-hydroxy- 3-methylurea (23 grams; 0.1 mol)in chloroform (200 ml.) and triethylamine (11 grams) are charged into aglass reaction vessel equipped with a mechanical stirrer. The mixture iscooled to a temperature of about C. and tetrahydropyran-4-carbonylchloride (15 grams; 0.1 mol) is slowly added thereto. After the additionis completed the mixture is allowed to warm up to room temperature andis stirred for a period of about 1 hour. After this time the reactionmixture is filtered to remove the triethylamine hydrochloride which hasformed, is washed with water and is dried over anhydrous magnesiumsulfate. The dried solution is stripped of solvent and the resultingresidue is recrystallized to yield the desired product 1 (2methoxy-4-chlorophenyl)-1-(4tetral1ydropyranyl carbonyloxy)-3-methylurea.

EXAMPLE 5 Preparation of 1-(4-dimethylaminophenyl)-1-picolinoyloxy-3-methylurea A solution of1-(4-dimethylaminophenyl)-1-hydroxy- 3-methylurea (21 grams; 0.1 mol) indichloromethane (150 ml.) and triethylamine (11 grams) are charged intoa glass reaction vessel equipped with a mechanical stirrer. The reactionmixture is cooled to a temperature of about 4 5 C. and picolinoylchloride (12.7 grams; 0.1 mol) is slowly added thereto. After theaddition is completed the mixture is warmed to room temperature and isstirred for a period of about 1 hour. After this time the mixture isfiltered to remove the triethylamine hydrochloride, is washed with waterand is dried over anhydrous magnesium sulfate. The dried solution isthen stripped of solvent under reduced pressure to yield the desiredproduct 1-(4- dimethylaminophenyl)-1-picolinoyloxy-3 methylurea as theresidue.

EXAMPLE 6 Preparation of 1-(3-trifluoromethylphenyl)-1-nicotinoyloxy-3-ethylurea A solution of1-(3-trifluoromethylphenyl)-1-hydroxy- 3-ethylurea (22 grams; 0.1 mol)in dichloromethane (200 ml.) and triethylamine (11 grams) are chargedinto a glass reaction vessel equipped with a mechanical stirrer. Thereaction mixture is cooled to a temperature of about 0 C. and nicotinoylchloride (12.7 grams; 0.1 mol) is slowly added thereto. After theaddition is completed the mixture is warmed to room temperature and isstirred for a period of about 1 hour. After this time the mixture isfiltered to remove the triethylamine hydrochloride, is Washed with waterand is dried over anhydrous magnesium sulfate. The dried solution isthen stripped of solvent under reduced pressure to yield the desiredproduct 1-(3-trifiuoron1ethylphenyl)-1-nicotinoyloxy-3 ethylurea as theresidue.

EXAMPLE 7 Preparation of 1-(3-Nitrophenyl)-l-isonicotinoyloxy-3-methylurea A solution of 1-(3-nitrophenyl)-1-hydroxy-3-methylurea (21grams; 0.1 mol) in carbon tetrachloride ml.) and triethylamine (11grams) are charged into a glass reaction vessel equipped with amechanical stirrer. The mixture is cooled to a temperature of about 10C. and isonicotinoyl chloride (12.7 grams; 0.1 mol) is slowly addedthereto. After the addition is completed the reaction mixture is warmedto room temperature and is stirred for a period of about 2 hours. Afterthis time the mixture is filtered to remove the triethylaminehydrochloride which is formed, is washed with water and is dried overanhydrous magnesium sulfate. The dried solution is then evaporated underreduced pressure to yield the desired product1-(3-nitrophenyl)-1-nicotinoyloxy-3-methylurea as the residue.

Additional compounds within the scope of the present invention which canbe prepared in a manner similar to that described in the foregoingexamples and which are presented by way of illustration and are notintended to limit the scope of this invention thereto are:

1-(3-ethyl-5-iodophenyl)-1- (B-furoyloxy)-3,3-diethylurea1-(4-allylphenyl)-1-(a-methyl-fl-furoyloxy)-3-isopropylurea1-(4-trichloromethylphenyl)-1- (a-chloro-fi-furoyloxy) -3 n-butylurea1-(2-ethoxy-4-isopropylphenyl) -1-pyrrolylcarbonyloxy-3 n-p entylurea 1-S-n-butyl-S-nitrophenyl) -1- (3-methyl-2-pyrrolylcarbonyloxy) -3-methylurea 1- (4-di-n-propylaminophenyl) -1- (3-chloro-2-pyrroly1-carbonyloxy -3 ,3-di-n-hexylurea 1-(4-pent-3-enylphenyl)-1-pyranylcarbonyloxy-3 -n-decylurea 1-(4-t-butyloxyphenyl)-1-(4-chloropicolinoyloxy) -3,3-

dimethylurea 1- (4-di-n-decylaminophenyl) 1 (5 -bromonicotinoyloxy) 3,3-diethylurea 1-( 3 -n-hexyloxyphenyl) -1-(2-n-propylisonicotinoyloxy)-3 methylurea 1- (4-n-decylphenyl) -1-(2-methyl-6-chloronicotinoyloxy) 3-n-pentylurea 1-(4-fiuorophenyl)-1-(3-methyl-2-thenoyloxy)-3-methylurea 1-(2,6-dimethoxy-4-chlorophenyl l-(4-methyltetrahydropyran-Z-ylcarbonyloxy)-3-methylurea.

For practical use as herbicides, the compounds of this invention aregenerally incorporated into herbicidal compositions which comprise aninert carrier and a herbicidally toxic amount of such a compound. Suchherbicidal compositions, which can also be called formulations, enablethe active compound to be applied conveniently to the site of the weedinfestation in any desired quantity. These compositions can be solidssuch as dusts, granules or Wettable powders; or they can be liquids suchas solutions, aerosols or emulsifiable concentrates.

For example, dusts can be prepared by grinding and blending the activecompound with a solid inert carrier such as the talcs, clays, silicas,pyrophyllite, and the like. Granular formulations can be prepared byimpregnating the compound, usually dissolved in a suitable solvent, ontoand into granulated carriers such as the attapulgites or thevermiculites, usually of a particle size range of from about 0.3 to 1.5mm. Wettable powders, which can be dispersed in water or oil to anydesired concentration of the active compound, can be prepared byincorporating wetting agents into concentrated dust compositions.

In some cases the active compounds are sufficiently soluble in commonorganic solvents such as kerosene or xylene so that they can be useddirectly as solutions in these solvents. Frequently, solutions ofherbicides can be dispersed under superatmospheric pressure as aerosols.However, preferred liquid herbicidal compositions are emulsifiableconcentrates, which comprise an active compound according to thisinvention and as the inert carrier, a solvent and an emulsifier. Suchemulsifiable concentrates can be extended with water and/or oil to anydesired concentration of active compound for application as sprays tothe site of the weed infestation. 'Ihe emulsifiers most commonly used inthese concentrates are nonionic or mixtures of nonionic with anionicsurface-active agents. With the use of some emulsifier systemsaninverted emulsion (water in oil) can be prepared for directapplication to weed infestation.

A typical herbicidal composition according to this invention isillustrated by the following example, in which the quantities are inparts by weight.

EXAMPLE 8 Preparation of a dust Product of Example 1 10 Powdered talc 90The above ingredients are mixed in a mechanical grinder-blender and areground until a homogeneous, freeflowing dust of the desired particlesize is obtained. This dust is suitable for direct application to thesite of the weed infestation.

The compounds of this invention can be applied as herbicides in anymanner recognized by the art. One method for the control of weedscomprises contacting the locus of said weeds with a herbicidalcomposition comprising an inert carrier and, as an essential activeingredient, in a quantity which is herbicidally toxic to said weeds, 3.compound of the present invention. The concentration of the newcompounds of this invention in the herbicidal compositions will varygreatly with the type of formulation and the purpose for which it isdesigned, but generally the herbicidal compositions will comprise fromabout 0.05 to about 95 percent by weight of the active compounds of thisinvention. In a preferred embodiment of this invention, the herbicidalcompositions will comprise from about 5 to about 75 percent by weight ofthe active compound. The compositions can also comprise such additionalsubstances as other pesticides, such as insecticides, nematocides,fungicides, and the like; stabilizers, spreaders, de-

activators, adhesives, stickers, fertilizers, activators, synergists,and the like.

The compounds of the present invention are also useful when combinedwith other herbicides and/or defoliants, desiccants, growth inhibitors,and the like in the herbicidal compositions heretofore described. Theseother materials can comprise from about 5% to about of the activeingredients in the herbicidal compositions. Use of combinations of theseother herbicides and/or de foliants, desiccants, etc. with the compoundsof the present invention provide herbicidal compositions which are moreeffective in controlling weeds and often provide results unattainablewith separate compositions of the individual herbicides. The otherherbicides, defoliants, desiccants and plant growth inhibitors, withwhich the compounds of this invention can be used in the herbicidalcompositions to control weeds, can include chlorophenoxy herbicides suchas 2,4-D, 2,4,5-T, MCPA, MCPB, 4(2,4- DB), 2,4-DEB, 4-CPB, 4-CPA, 4-CPP,2,4,5-TB, 2,4,5- TES, 3,4-DA, silvex, and the like; carbamate herbicidessuch as IPC, CIPC, swep, barban, BCPC, CEPC, CPPC, and the like;thiocarbamate and dithiocarbamate herbicides such as CDEC, niethamsodium, EPTC, diallate, PEBC, perbulate, vernolate, and the like;substituted urea herbicides such as norea, siduron, dichloral urea,chloroxuron, cycluron, fenuron, monuron, monuron TCA, diuron, linuron,monolinuron, neburon, buturon, trimeturon, and the like; symmetricaltriazine herbicides such as simazine, chlorazine, atratone, desmetryne,norazine, ipazine, prometryn, atrazine, trietazine, simetone, prometone,propazine, ametryne, and the like; chloroacetamide herbicides such asalpha-chloro-N,N-dimethylacetamide, CDEA, CDAA,alpha-chloro-N-isopropylacetamide, 2- chloro-N-isopropylacetanilide, 4(chloroacetyl)morpholine, l-(chloroacetyl)piperidine, and the like;chlorinated aliphatic acid herbicides such as TCA, dalapon,2,3-dichloropropionic acid, 2,2,3-TPA, and the like; chlorinated benzoicacid and phenylacetic acid herbicides such as 2,3, 6-TBA, 2,3,5,6-TBA,dicamba, tricamba, amiben, fenac, PBA,2-methoxy-3,6-dichlorophenylacetic acid 3-methoxy-2,6-dichlorophenylacetic acid, 2-methoxy-3,5,6-trichlorophenylaceticacid, 2,4-dichloro-3-nitrobenzoic acid, and the like; and such compoundsas aminotriazole, maleic hydrazide, phenyl mercuric acetate, endothalbiuret, technical chlordane, dimethyl 2,3,5,6-tetrachloroterephthalate,diquat, erbon, DNC, DNBP, dichlobenil, DPA, diphenamid, dip-ropalin,trifluralin, solan, dicryl, merphos, DMPA, O-S-dimethyltetrachlorothioterephthalate, methyl 2,3,5,6tetrachloro-N-methoxy-N-methylterephthalamate, 2-[(4chloro-0-tolyl)-oxy]-N-methoxyacetamide, DSMA, MSMA, potassium azide,acrolein, benefin, bensulide, AMS, bromacil, bromoxynil, cacodylic acid,CMA, CPMF, cypromid, DCB, DCPA, dichlone, diphenatril, DMTT, DNAP, EBEP,EXD, HCA, ioxynil, IPX, isocil, potassium cyanate, MAA, MAMA, MCPES,MCPP, MH, molinate, NPA, OCH, paraquat, PCP, picloram, DPA, PCA,pyrichlor, sesone, terbacil, terbutol, TCBA, brominil, CP-50144,H-l76-1, H-732, M-2901, planavin, sodium tetraborate, calcium cyanamid,DEF, ethyl xanthogen disulfide, sindone, sindone B, propanil, and thelike.

Such herbicides can also be used in the methods and compositions of thisinvention in the form of their salts, esters, amides and otherderivatives whenever applicable to the particular parent compounds.

Weeds are undesirable plants growing where they are not wanted, havingno economic value, and interfering with the production of cultivatedcrops, with the growing of ornamental plants, or with the welfare oflivestock. Many types of weeds are known, including annuals such aspigweed, lambs-quarters, foxtail, crabgrass, wild mustard, fieldpennycress, ryegrass, goose-grass, chickweed, wild oats, velvet leaf,purselane, barnyard grass, smartweed, knotweed, cocklebur, wildbuckwheat, kochia, medic, corn cockle, ragweed, sowthistle, coffee-Weed,

croton, cuphea, dodder, fumitory, groundsel, hemp nettle, knowel,spurge, spurry, emex, jungle rice, pondweed, dog fennel, carpetweed,morning glory, bedstraw, ducksalad and naiad; biennials such as wildcarrot, matricaria, wild barley, campion, chamomile, burdock, mullein,roundleaved mallow, bull thistle, hounds-tongue, moth mullein and purplestar thistle; or perennials such as white cockle, perennial rye-grass,quackgrass, Johnson grass, Canada thistle, hedge bindweed, Bermudagrass, sheep sorrel, curly dock, nutgrass, field chickeed, dandelion,campanula, field bindweed, Russian knapweed, mesquite, toadflax, yarrow,aster, gromwell, horsetail, ironweed, ses'- bania, bulrush, cattail andwinter-cress.

Similarly, such Weeds can be classified as broadleaf or grassy weeds. Itis economically desirable to control the growth of such weeds withoutdamaging beneficial plants or livestock.

The new compounds of this invention are particularly valuable for weedcontrol because they are toxic to many species and groups of weeds whilethey are relatively nontoxic to many beneficial plants. The exact amountof compound required will depend on a variety of factors, including thehardiness of the particular weed species, weather, type of soil, methodof application, the kind of beneficial plants in the same area, and thelike. Thus, while the application of up to only about one or two ouncesof active compound per acre may be sufficient for good control of alight infestation of weeds growing under adverse conditions, theapplication of ten pounds or more of active compound per acre may berequired for good control of a dense infestation of hardy perennialweeds growing under favorable conditions.

The herbicidal toxicity of the new compounds of this invention can beillustrated by many of the established testing techniques known to theart, such as preand post-emergence testing.

The herbicidal activity of the compounds of this invention wasdemonstrated by experiments carried out for the pre-emergence control ofvarious Weeds. In these experiments small plastic greenhouse pots filledwith dry soil were seeded with the weed seeds. Twenty-four hours or lessafter seeding the pots were sprayed with water until the soil was wetand 1-(3,4-dichlorophenyl)-1-(u-furoyloxy)-3-methylurea formulated as anaqueous emulsion of an acetone solution containing emulsifiers wassprayed at the indicated concentrations on the surface of the soil.

After spraying, the soil containers were placed in the greenhouse andprovided with supplementary heat as required and daily or more frequentwatering. The plants were maintained under these conditions for a periodof from 15 to 21 days, at which time the condition of the plants and thedegree of injury to the plants was rated on a scale of from to 10, asfollows: 0=no injury; 1, 2=slight injury; 3, 4=moderate injury; 5,6=moderately severe injury; 7, 8, 9=severe injury and 10=death. Averagevalues are given for data obtained from replicate experiments. Theeffectiveness of these compounds is demonstrated by the following data:

The herbicidal activity of the compounds of this invention was alsodemonstrated by experiments carried out for the post-emergence controlof various needs. In these experiments the compound1-(3,4-dichlorophenyl)- 1-(a-furoyloxy)-3-methylurea was formulated asan aque ous emulsion and sprayed at the indicated dosage on the foliageof various weeds that had attained a prescribed size. After spraying,the plants were placed in a greenhouse and watered daily or morefrequently. Water was not applied to the foliage of the treated plants.The severity of the injury was determined 10 to 15 days after treatmentand was rated on the scale of from 0 to 10 heretofore described. Theeffectiveness of these compounds is demonstrated by the following data:

wherein X is selected from the group consisting of lower alkyl, loweralkenyl, chlorine, bromine, lower haloalkyl, lower alkoxy, nitro and di(lower alkyl)amino; n is an integer from O to 3; R and R areindependently selected from the group consisting of hydrogen and loweralkyl; and Y is a substituted or unsubstituted heterocyclic ringconsisting of furan and tetrahydrofuran wherein substituents areselected from the group consisting of lower alkyl, chlorine and bromine.

2. The compound of Claim 1, 1-(3,4-dichlor0phenyl)- 1-( a-fUI'OYlOXY)-3-methylurea.

References Cited FOREIGN PATENTS 6/1966 U.S.S.R.

NATALIE TROUSOF, Primary Examiner B. DENTZ, Assistant Examiner US. Cl.X.R.

7188, 90, 94, 200-239 R, 295 E, 326.2, 295.50, 332.2 C, 345.7

1. A COMPOUND OF THE FORMULA